Polycyclic ethyl alkylamide melatonergic agents

Abstract

Novel polycyclic ethyl alkylamides of formula I are active as melatonergic agents. ##STR1## wherein Z=CH (when a double bond is present) or (CH 2 ) n , wherein n is 1-4; X=O, CH 2 , or CH (when a double bond is present); R=C 1-6 alkyl, C 3-6 cycloalkyl, or C 1-3 haloalkyl, C 2-6 alkenyl, C 2-4 alkoxyalkyl, C 1-4 trifluoromethylalkyl, C 1-6 aminoalkyl; and Y=H, C 1-6 alkoxy or halogen.

We claim: 
     
       1. A compound of Formula I or a pharmaceutically acceptable solvate thereof, Formula I being: ##STR13## wherein Z=CH (when a double bond is present) or (CH 2 ) n , wherein n is 1-4; X=O, CH 2 , or CH (when a double bond is present);   R=C 1-6  alkyl, C 3-6  cycloalkyl, or C 1-3  haloalkyl, C 2-6  alkenyl, C 2-4  alkoxyalkyl, C 1-4  trifluoromethylalkyl, C 1-6  aminoalkyl; and   Y=H, C 1-6  alkoxy or halogen.   
     
     
       2. The compound of claim 1 wherein Y is H and Z is CH 2 . 
     
     
       3. The compound of claim 2 wherein X is CH 2 . 
     
     
       4. The compound of claim 3 wherein R is C 1-6  alkyl. 
     
     
       5. The compound of claim 4, N- 2-(2,10-dihydro-1H-fluoreno 2,1-b!furan-10-yl)ethyl!propanamide. 
     
     
       6. The compound of claim 1 wherein Y is OCH 3  and Z is CH 2 . 
     
     
       7. The compound of claim 6 wherein X is O. 
     
     
       8. The compound of claim 7 wherein R is C 1-6  alkyl. 
     
     
       9. The compound of claim 8, N- 2-(8-Methoxy-10H-fluoreno 1,2-d!-1,3-dioxol-10-yl)ethyl!propanamide. 
     
     
       10. A method of treating a sleep disorder in a patient in need of treatment comprising administering to said patient a therapeutically effective amount of a compound of claim 1. 
     
     
       11. A composition useful for treating a sleep disorder comprising a therapeutically effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier. 
     
     
       12. A method of treating circadian rhythm disorder in a patient in need of treatment comprising administering to said patient a therapeutically effective amount of a compound of claim 1. 
     
     
       13. A composition useful for treating a circadian rhythm disorder comprising a therapeutically effective amount of a compound of claim 1 and of a pharmaceutically acceptable carrier.